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2‐Thioxo‐1,3‐thiazepan‐4‐ones, a novel class of cyclic dithiourethanes with a 7‐membered ring system
Author(s) -
Hanefeld Wolfgang,
Schütz Harald
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360509
Subject(s) - chemistry , ring (chemistry) , butyric acid , isothiocyanate , medicinal chemistry , cyclic amines , stereochemistry , organic chemistry , catalysis
Reaction of isothiocyanates 1 with γ‐thiobutyrolactone ( 2 ) in alkaline medium yielded 4‐thiocarbamoylthiobutyric acids 3 after acidification, which could be cyclized to the 2‐thioxo‐1,3‐thiazepan‐4‐ones 6 . Additional reactions were observed with the formation of 6t from p ‐phenylenediisothiocyanate ( 1s ) and with the formation of 6w from benzyl isothiocyanate ( 1t ). 3‐Acetylamino‐γ‐thiobutyrolactone ( 7 ) could also be used in this reaction yielding the butyric acid derivatives 3u‐3w . Cyclization yielded the 1,3‐thiazepane derivatives 6x, y which rearranged under ring contraction to the 1,3‐thiazinanes 8a, b .